This invention relates to certain novel N-hydroxy-N'-sulfonylguanidine compounds, to compositions containing such compounds, and to a method of use of such compositions to control the growth of undesired vegetation.
U.S. Pat. No. 4,127,405 issued Nov. 28, 1978 discloses substituted triazinyl arylsulfonylurea compounds of the following formula: ##STR1## while U.S. Pat. No. 4,169,719 issued Oct. 2, 1979 discloses substituted pyrimidinyl arylsulfonylurea compounds of the following formula: ##STR2## The triazine and pyrimidine compounds within the scope of the '405 and '719 patents include those wherein W can be oxygen or sulfur.
U.S. Pat. No. 4,310,346 issued Jan. 12, 1982 discloses sulfonylisothiourea compounds of the formula ##STR3## wherein B is C.sub.1 -C.sub.6 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 Q, ##STR4## where Q is CO.sub.2 -C.sub.1-3 alkyl, ##STR5## phenyl, phenyl substituted with chlorine, CN, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, OR.sub.11, where R.sub.11 is C.sub.1 -C.sub.4 alkyl, --CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 or --CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3.
South African Pat. No. 79/2657, published Jun. 30, 1980 discloses sulfonylisothiourea compounds of the formula ##STR6## wherein R.sub.2 is C.sub.1 -C.sub.20 alkyl; CH.sub.2 CH.sub.2 OCH.sub.3 ; CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ; CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ; CH.sub.2 OA' where A' is C.sub.1 -C.sub.12 alkyl, --CH.sub.2 CH.sub.2 OCH.sub.3, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, phenyl or phenyl substituted with 1-2 NO.sub.2, 1-2 Cl, or 1-2 CH.sub.3 ; CH.sub.2 A, ##STR7## where A is CO.sub.2 (H, C.sub.1 -C.sub.4 alkyl), ##STR8## phenyl, CN, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkynyl, phenyl substituted with 1-2 CH.sub.3, 1-2 NO.sub.2, 1-2 OCH.sub.3, 1-2 chlorine or phenoxy.
U.S. Pat. No. 4,301,286 issued Nov. 17, 1981 discloses O-alkylsulfonylisoureas of the formula ##STR9## wherein W is Cl, Br or OR.sup.12 ; and
R.sup.12 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, (CH.sub.2).sub.3 OCH.sub.3, benzyl, CHR.sup.13 CO.sub.2 R.sup.14, where R.sup.13 is H or CH.sub.3 and R.sup.14 is C.sub.1 -C.sub.4 alkyl. PA1 R.sub.2 and R.sub.3 is a lower alkyl or lower alkoxy group; and PA1 R.sub.4 is a hydrogen atom, a lower alkyl group or a lower alkoxy group. PA1 R' is OH, OC(O)R.sub.1, OC(O)NR.sub.2 R.sub.3, OCOR.sub.4, OR.sub.3 or R.sub.3 ; PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.2 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.3 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl; PA1 L is ##STR12## R.sub.5 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, F, Cl, Br, NO.sub.2, CF.sub.3, CO.sub.2 R.sub.19, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.22, S(O).sub.n R.sub.23, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR13## R.sub.6 is H, F, Cl, Br, CF.sub.3, CH.sub.3, OCH.sub.3, SCH.sub.3 or OCF.sub.2 H; PA1 R.sub.7 is H, CH.sub.3, OCH.sub.3, F, Cl, Br, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3 or S(O).sub.n CH.sub.3 ; PA1 R.sub.8 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.23 ; PA1 R.sub.9 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.19, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.23 ; PA1 R.sub.10 is Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3, SO.sub.2 CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sub.11 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.12 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.13 is H or CH.sub.3 ; PA1 R.sub.14 is H or CH.sub.3 ; PA1 R.sub.15 is H or CH.sub.3 ; PA1 R.sub.16 is CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.17 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.18 is H or CH.sub.3 ; PA1 R.sub.19 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.20 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.21 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.22 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; PA1 R.sub.23 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 m is 0 or 1; PA1 n is 0 or 2; PA1 Q.sub.1 is O, S, SO.sub.2 or NR.sub.17 ; PA1 Q.sub.2 is O, S or NR.sub.17 ; and PA1 W is O, S or SO.sub.2 ; PA1 A is ##STR14## X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F or CF.sub.3 ; PA1 Y is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 CH.sub.3, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, CR.sub.24 (QCH.sub.3).sub.2, ##STR15## or CR.sub.24 (QCH.sub.2 CH.sub.3).sub.2 ; Q is O or S; PA1 R.sub.24 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is CH.sub.2 or O; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.3 is OCH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 (1) the total number of carbon atoms of R.sub.20 and R.sub.21 is less than or equal to four; PA1 (2) when m is 1, then R.sub.13 is H; PA1 (3) when L is L-17, then R.sub.17 and R.sub.18 are not simultaneously H; PA1 (4) when X is Cl, F or Br, then Z is CH and Y is OCH.sub.3, OCH.sub.2 CH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (5) when R' is C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkyl, and L is L-1 then either R.sub.5 is other than C.sub.6 H.sub.5 or R.sub.6 is other than H; and PA1 (6) when X or Y is OCF.sub.2 H, then Z is CH. PA1 R, L and A are defined for Formula I; PA1 (1) when L is L-1 and A is A-1, R.sub.5 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, OSO.sub.2 R.sub.22, S(O).sub.n CH.sub.2 CH.dbd.CH.sub.2, WCF.sub.2, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR17## (2) when L is L-1 and A is A-2 or A-3, then R.sub.5 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, OSO.sub.2 R.sub.22, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR18## (3) when L is L-3 and A is A-1, A-2 or A-3, then R.sub.8 is SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3 or SO.sub.2 R.sub.23 ; PA1 (4) when L is L-4, L-5 or L-6 and A is A-1, A-2 and A-3, then R.sub.9 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.23 ; and PA1 (5) when L is L-2, then A is A-5 or A-6. PA1 (1) Compounds of Formula I where R is H, R' is OH and A is A-1. PA1 (2) Compounds of Formula I where R is H, R' is C.sub.1 -C.sub.2 alkoxy and A is A-1. PA1 (3) Compounds of Preferred 1 where Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, OCH.sub.2 CF.sub.3 or CH(OCH.sub.3).sub.2 and X is CH.sub.3, OCH.sub.3, Cl or CF.sub.3. PA1 (4) Compounds of Preferred 2 where Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, OCH.sub.2 CF.sub.3 or CH(OCH.sub.3).sub.2 and X is CH.sub.3, OCH.sub.3, Cl or CF.sub.3. PA1 (5) Compounds of Preferred 3 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17. PA1 (6) Compounds of Preferred 5 where L is L-1, R.sub.5 is OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, NO.sub.2, CF.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.22, S(O).sub.n R.sub.23, OCF.sub.2 H, SCF.sub.2 H, C.sub.6 H.sub.5, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH. ##STR19## R.sub.22 is C.sub.1 -C.sub.3 alkyl; R.sub.23 is CH.sub.3 and n is 2. PA1 (7) Compounds of Preferred 4 where L is L-1, L-2, L-3, L-5, L-8, L-10, L-11, L-16 or L-17. PA1 (8) Compounds of Preferred 7 where L is L-1, R.sub.5 is OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, NO.sub.2, CF.sub.3, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.22, S(O).sub.n R.sub.23, OCF.sub.2 H, SCF.sub.2 H, C.sub.6 H.sub.5, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, ##STR20## R.sub.22 is C.sub.1 -C.sub.3 alkyl; R.sub.23 is CH.sub.3 and n is 2. PA1 (9) Compounds of Preferred 5 where L is L-2 and R.sub.7 is Cl, CH.sub.3, OCH.sub.3, SCH.sub.3 or Br. PA1 (10) Compounds of Preferred 5 where L is L-3 and R.sub.8 is Cl, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2. PA1 (11) Compounds of Preferred 5 where L is L-5 and R.sub.9 is CO.sub.2 CH.sub.3 or CO.sub.2 CH.sub.2 CH.sub.3. PA1 (12) Compounds of Preferred 5 where L is L-8. PA1 (13) Compounds of Preferred 5 where L is L-10. PA1 (14) Compounds of Preferred 5 where L is L-11. PA1 (15) Compounds of Preferred 5 where L is L-16. PA1 (16) Compounds of Preferred 5 where L is L-17. PA1 (17) Compounds of Preferred 7 where L is L-2 and R.sub.7 is Cl, CH.sub.3, OCH.sub.3, SCH.sub.3 or Br. PA1 (18) Compounds of Preferred 7 where L is L-3 and R.sub.8 is Cl, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2. PA1 (19) Compounds of Preferred 7 where L is L-5 and R.sub.9 is CO.sub.2 CH.sub.3 or CO.sub.2 CH.sub.2 CH.sub.3. PA1 (20) Compounds of Preferred 7 where L is L-8. PA1 (21) Compounds of Preferred 7 where L is L-10. PA1 (22) Compounds of Preferred 7 where L is L-11. PA1 (23) Compounds of Preferred 7 where L is L-16. PA1 (24) Compounds of Preferred 7 where L is L-17. PA1 (25) Compounds of Formula II where R is H and A is A-1. PA1 (26) Compounds of Preferred 25 where Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, OCH.sub.2 CF.sub.3 or CH(OCH.sub.3).sub.2 and X is CH.sub.3, OCH.sub.3, Cl or CF.sub.3 ; PA1 (27) Compounds of Preferred 26 where L is L-1 and R.sub.5 is OSO.sub.2 R.sub.22, SO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, OCF.sub.2 H, SCF.sub.2 H, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.H, ##STR21## or C.sub.6 H.sub.5.
South African patent application No. 84/4808 discloses herbicidal sulfonamides of formula ##STR10## wherein R.sub.1 is a phenyl or phenoxy group; each of
The compounds taught in the above references are useful as general or selective herbicides having both preemergent and postemergent herbicidal activity or plant growth regulant activity.